Sodium Chloride → HCID 70235568, compound
Reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]1[C@@H:11]([CH3:12])[C@@H:10]([CH2:13]/[CH:14]=[CH:15]/[Sn](CCCC)(CCCC)CCCC)[C:9]1=[O:29].Br[C:31]1[S:32][CH:33]=[CH:34][CH:35]=1.[OH-].[NH4+].[Cl-].[Na+]>CN(C)C=O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][N:8]1[C@@H:11]([CH3:12])[C@@H:10]([CH2:13]/[CH:14]=[CH:15]/[C:31]2[S:32][CH:33]=[CH:34][CH:35]=2)[C:9]1=[O:29]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
To a solution of (3R,4S)-1-(2-tetrahydropyranyloxy)-3-((2E)-3-tributylstannyl-2-propene-1-yl)-4-methylazetidin-2-one (400 mg, 0.78 mmol) in 1 mL of dimethylformamide is added 2-bromothiophene (152 mg, 0.93 mmol) and triphenyphosphine palladium (II) dichloride (27 mg, 0.04 mmol). The resulting solution is heated at 80° C. for 2 h, then 0.5 mL ammonium hydroxide is added. The reaction mixture is poured into saturated sodium chloride solution (20 mL) and extracted with 1:1 ethyl acetate/hexane (50 mL). The combined organic layers were dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and purified by silica gel chromatography (elution with 3:1 hexanes-ethyl acetate) to provide (3R,4S)-1-(2-tetrahydropyranyloxy)-3-((2E)-3-(thiophene-2-yl)-2-propene-1-yl)-4-methylazetidin-2-one as an oil (130 mg, 54% yield).
Workup
- extractionextracted with 1:1 ethyl acetate/hexane (50 mL)
- dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
- concentrationconcentrated under reduced pressure
- custompurified by silica gel chromatography (elution with 3:1 hexanes-ethyl acetate)
Sources & evidence
- ORD record
- ord-69ec5d239fd84559988698d8bc6336a5
- Source dataset
- uspto-grants-2001_01
- Patent number
- US06172064B2
Reaction notes
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